This 37-Year-Old Makes 5 Figures/Month Renting Vacation Homes in Arkansas

Garrett Ham had experience in real estate. He worked in the industry and obtained his license. And while in the Air Force, he started purchasing properties and then renting them out long-term.

When he decided to return to his native Arkansas, he ended up investing in a short-term rental. He had such success that he turned it into a business: Weekender Management.

Today he’s earning 5 figures per month managing 41 properties, and he has plans to add another 8 to his portfolio in the near future.

Keep reading to find out:

• How he got started in real estate
• Why he was hesitant to work with short-term rentals
• What he’s learned while running that business
• How he identifies the perfect client
• How much he works per week
• His marketing strategy for getting new clients
• The resources he recommends
• His biggest challenge
• His greatest accomplishment
• His advice for other entrepreneurs

Meet Garrett Ham

My name is Garrett, and I’m 37 years old. I hold a Bachelor of Arts from Ouachita Baptist University, a Juris Doctor from the University of Arkansas, and a Master of Divinity from Yale University. I hold both a license to practice law and a principal real estate broker’s license in Arkansas. 

After law school, I worked in Walmart’s real estate division for three years. During that time, I also joined the Army National Guard as a JAG officer. I left Walmart in 2013 to work in private practice before becoming a prosecutor in Benton County Arkansas. 

In 2015, I joined the active duty Air Force, spending four years as a full-time JAG officer. In that position, I was primarily responsible for military justice matters, including serving as a prosecutor in courts-martial. 

Most of my cases revolved around sexual assault and child pornography charges. I spent three years at Yale after leaving the military, and I founded my company, Weekender Management, with my sister during my last year there.

After graduation, I moved back home to Bentonville, Arkansas, where I run my business full-time.

My wife and I have been married for fifteen years, and we have two children: a daughter, who is eleven, and a son, who is nine.

Why He Created Weekender Management

This business was the result of an unexpected opportunity. 

I had a background in real estate, and I began investing in real estate myself when I was in the military. I would purchase a new home at each duty assignment, and then I would rent out when the Air Force moved me elsewhere. By the time I left the Air Force, I had three rental properties. 

While I was at Yale, I knew I wanted to return back home to Arkansas after graduation. So, I began looking to purchase my fourth rental property near home. The real estate market in northwest Arkansas had grown so hot, however, that it was difficult to find a property that would have a cash flow. 

I was finally able to find one that the owner was using as a short-term rental. It was the only property that I found that would have cash flow, but it would only provide a cash flow as a short-term rental. Short-term rentals were never something that I had ever considered, but I decided to give it a shot. 

My sister had just sold off a business that she had founded—a glamping company where she would set up luxury tents for clients wherever they wanted to stay—so I asked her to help me run my short-term rental until I could return home.

As we started gaining some success with the property, some people started asking us to help them with theirs, and we decided to start Weekender Management as a result.

We are a full-service short-term rental management company. We handle every aspect of running a short-term rental, from marketing, guest screening and communications, evaluating the market and setting prices, cleaning properties between guests, and just about anything in between. Our clients are able to receive returns on their investment without having to expend any of the effort that running a short-term rental requires.

It’s been a learning process along the way. 

We are always trying to improve how we do things, and that has led to some bumps along the way. We learned that there are some kind of clients that are a good fit for us and some that aren’t. I’d say most of our failures have revolved around failing to appreciate that in the beginning. 

When you’re just starting out, you want to say yes to everything, but that’s rarely a winning strategy. If you take on the wrong types of client, you’re unhappy and the client is unhappy. 

So, learning to identify who is a good fit for our offerings and helping those who aren’t find some alternative companies that may be a better fit has been critical to our growth. 

In that vein, we have found that our ideal client is an investor who is focused on maximizing the return on their property, regardless of whether they are new to the investment game or a seasoned professional. 

They prioritize guest satisfaction over sentimental attachment to the property and are open to decorating and pricing strategies that will appeal to potential guests. We are not a good fit for those who have strict rules for guests to follow or want to set minimum nightly rates based on their personal beliefs about the value of their property.

How Much Money Garrett is Making

We’re making 5 figures per month. It took about 18 months to reach that revenue level. I spend about 60 to 70 hours per week on the business.

His Main Marketing Strategy

We utilize Google ads to attract new clients, but we rely primarily on word of mouth and referrals. We currently only spend about $150 per month on Google ads. 

There was a time when we were spending about $1,000 per night, but we were getting so many leads and bringing on so many clients so quickly, we had to scale back just to ensure we could keep up with our incoming business. We still get a steady flow of inquiries even at the lower spending level. 

We currently do all of our marketing ourselves. I discovered Google Ads by watching hours of YouTube videos and reading books about it. We’re looking to outsource this process in the near future, however. 

His Views on SEO

We utilize SEO, but we have not put a lot of focus in that direction. As we have received most of our business from referrals and Google ads, we’ve focused most of our efforts to date in that direction. 

His Email List

We have an email list and grow it by asking our guests to provide theirs. We also give away educational material on our website in exchange for an email address. We specifically offer a short ebook outlining five tips for becoming a successful Airbnb host for anyone who signs up to our mailing list.

Garrett’s Favorite Resources

My advice is to find as much educational material as possible, particularly books, and prioritize learning. 

Find podcasts by experts in your niche, “Get Paid For Your Pad,” and anything from Bigger Pockets, for example, is particularly valuable in my field. 

Take a basic accounting course at a local community college or university. Make sure you understand basic concepts such as the time value of money, and you can’t go wrong reading anything by Mike Michalowicz. 

Finally, while it requires a significant investment, take courses geared toward your particular niche. I’ve taken training from BeyondBnb and LegendsX, which are specifically designed for short-term rental owners, and was able to learn and immediately implement a lot of valuable advice that would have taken me years to learn on my own.

His Biggest Challenge

This would have to be learning what’s worth spending money on and what’s not. 

For example, we hired an accounting firm to help us draft owners’ statements every month. They did a good job, but they were very expensive. And we ended up having to audit the statements before they went out anyway. So, they weren’t saving us a whole lot of time and we were spending a whole lot of money. 

I’ve had enough graduate-level accounting courses to be able to do this myself, so that’s what I’ve started doing. We then hired a much cheaper bookkeeper to keep our books. While we will need to outsource this again soon, we’ve become a lot more aware of when a service brings real value and when the value it brings is less than what’s being expended.

“You’ve got to spend money to make money” may be true in some contexts, but it’s not universally applicable. When you’re just getting started, a better mantra is “You’ve got to spend money to go bankrupt.” 

If the answer is “No,” spend it. If the answer is “Yes,” which it almost always will be, then don’t. Be honest with yourself, and definitely don’t spend money on things just because you think you need them to be a legitimate business.

His Greatest Accomplishment

That would be surviving. With so many businesses failing within the first year, just surviving and turning a profit at this point seems like a huge accomplishment. 

What He Wishes He Knew When He Started

Be very careful how you spend money, and spend as little as possible. Make sure your spending is such that you have a profit from the very beginning. 

His Advice for Other Entrepreneurs

To succeed, you have to be a risk-taker, but you must be smart about it. Only spend money on something if failing to do so will hurt your business.